Acetic Anhydride → HCID 21409886, compound

HRID 2071985Notes

Reaction equation

HRID 2071985 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[CH3:8][NH:9][CH2:10][C:11]1([N:17]([CH3:19])[CH3:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)=O>[CH:5]([N:9]([CH3:8])[CH2:10][C:11]1([N:17]([CH3:19])[CH3:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21409873HCID 21409873, compound

Product 1

HCID 21409886HCID 21409886, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

Formic acid (6.9 g. 0.15 mole) and acetic anhydride (15.3 g, 0.15 mole) were mixed without cooling and kept at room temperature for 1 hr. 1-methylaminomethylcyclohexyldimethylamine (5.9 g, 0.034 mole) was dissolved in formic acid (12 ml) and the formylating mixture (16 ml) added slowly. This produced vigorous effervesence and a temperature rise to 75°. The mixture was then left at room temperature for 2 hr. and then heated on a water bath at 55° for 0.75 hr. The solvents were removed under reduced pressure to give an amber oil (5.32 g, 77.7%) which crystallised as colourless prisms of 1-(N-formyl-1-methylaminomethyl) cyclohexyldimethylamine from light petroleum (b.p. 60°-80° ), m.p. 59°-60°.

Workup

  1. temperaturewithout cooling
  2. customto 75°
  3. waitThe mixture was then left at room temperature for 2 hr
  4. temperatureand then heated on a water bath at 55° for 0.75 hr
  5. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-b5a0ec427ed2497f869cfea0489d07aa
Source dataset
uspto-grants-1977_09
Patent number
US04049663

Reaction notes

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